tert-Butyl 4-(2-bromoethyl)piperazine-1-carboxylate → Tert-butyl 4-(2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)ethyl)piperazine-1-carboxylate

HRID 1667130Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[CH2:12][CH2:11][NH:10][C:9]2=[O:13])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]1>O1CCCC1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:12][CH2:11][N:10]([CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH2:32][CH2:31]3)[C:9]2=[O:13])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 3,3-bis(4-fluorophenyl)pyrrolidin-2-one (Example 58B, 1.37 g, 5.00 mmol) in tetrahydrofuran (30 mL) was added potassium t-butoxide (1.0 M in tetrahydrofuran) (7.5 mL, 7.5 mmol) followed by the product from Example 63A (1.47 g, 5.00 mmol). The reaction mixture was heated at 75° C. for 18 hours. The reaction was concentrated, diluted with ethyl acetate, washed with water and brine, dried with MgSO4, filtered and concentrated. The residue was purified with silica gel chromatography eluting with 3% methanol/dichloromethane to give the title compound. MS (DCI) m/z 486.3 (M+H)+.

Workup

concentrationThe reaction was concentrated
additiondiluted with ethyl acetate
washwashed with water and brine
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified with silica gel chromatography
washeluting with 3% methanol/dichloromethane

Sources & evidence

ORD record: ord-2e93e0abe194410db3b05be3b3510765
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044069B2

Reaction notes

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